Originally published by Esquire
So you feel like you’re too old for abackpack, but you’re not quite ready to go full lawyer-mode and commit to a hand-heldbriefcase. There’s really only one move left: Get a messenger bag. Though, truthfully, messenger bag and briefcase can be used interchangeably these days. What we’re talking about here is a bit more utilitarian. There should be a shoulder strap and enough space inside for more than just work items.
The messenger bag does carry a certain academic, bookish energy. But the modern messenger bag is as much for CFOs as it is teaching assistants. They’re practical, polished, and ideal for commuting, with enough room for yourlaptop, charger,notebook,AirPods, keys,pens, and whatever else you need—minus the kiddy look of abackpack.
- The Best Affordable Messenger BagRains Messenger BagRead more
The Best Affordable Messenger Bag
- The Best Looking $200 Messenger BagSamsonite Classic Leather FlapoverRead more
The Best Looking $200 Messenger Bag
Samsonite Classic Leather Flapover
- Our Favorite Messenger BagBennett Winch Leather BriefRead more
Our Favorite Messenger Bag
Bennett Winch Leather Brief
We love a simpleleather messenger bagthat dresses up, and we’ve also rounded up some great options in other materials, including awaterproofpick for the guy who commutes rain or shine. These bags look sharp, and so will you when you’re wearing one.
For rainy days, or really any weather, the Rains Messenger Bag is the easy pick. It’s sleek, modern, and water-resistant, but it never looks too tech-y. That comes from the classic shape with details that keep it interesting—like a cool carabiner closure on the front flap and waxy polyester body. It has a little bit of bike messenger edge, but it looks sharper than a backpack ever will in a serious investor meeting. And it does it at a price that won’t make your wallet cry.
Samsonite Classic Leather Flapover
If you want that old-fashioned double-buckle look, nothing beats Samsonite’s Classic Leather Flapover. It’s less expensive than most of the other options on this list but holds up pretty well—it even hastwolaptop pockets, just in case, you know, you have two laptops you need to bring with you. It’s a timeless look with a clever, modern design.
Bennett Winch Leather Brief
A favorite of commerce editor Luke Guillory, this Bennett Winch bag is the perfect luxury option. It’s a modern upgrade on the classic messenger silhouette, with concealed pockets for your phone and wallet, a laptop compartment inside, and a luggage sleeve that makes airport schlepping easy.
Beautiful black Tuscan leather, sturdy zippers, and an twill interior that’s as polished as the outside make it a go-to if you mean business. And then there’s the fold-over flap, which gives the whole thing a slightly bookish, professor-on-sabbatical energy—in other words, it makes you look smart, even before you say a word.
Coach League Messenger Bag
If you want a messenger bag that keeps things lean, the Coach League Messenger Bag is the move. It’s simple, elegant, and gets the job done without any unnecessary fuss. It might not be the one you grab when you need to haul a laptop and your entire workday on your shoulder—but for a tablet, a notebook, and all the small essentials, it definitely has enough room. It’s clean and compact, with a quick-clip buckle for easy opening and closing.
Filson Rugged Twill Original Briefcase
If you work in a creative field that doesn’t require you to dress up—or anywhere that doesn’t require you to dress up, these days—this is the messenger bag for you. Instead of being all-over leather, it’s made from rugged cotton twill with leather handles and a removable shoulder strap. It’s heavy duty and can fit a 15-inch laptop and whatever else you need for the day. We like this tan colorway, but it also comes in black, navy, and green—all great options, all still made in the U.S.A.
Tecovas Bartlett Slim Briefcase
If style is the priority, Tecovas’ Bartlett Slim Briefcase is the one to beat. You carry to this if you work in Austin or Los Angeles, somewhere where you don’t dress up all that much. It’s polished enough for work, relaxed enough to carry straight to the bar when your “remote office” starts serving happy hour. It’s masculine without feeling bulky, made from cowhide leather that’ll only look better with age, and roomy enough to fit up to a 16-inch laptop. Bring this bag with you when you want the compliments to roll in.
Métier Closer Briefcase
If you want the luxury pick, it’s Métier. This is a bag for serious work, the kind where looking the part matters. Métier also generously sizes the “All Day” version of the Closer, so you can carry more than just your laptop and small essentials.
It’s straight up gorgeous, and Esquire’s shopping desk is preferential to Métier, regardless what sort of bags we’re talking about. We’ve included the brand in our most recentTravel Awards, and Krista Jones, Esquire’s senior director of commerce and partnerships, has writtenan entire story on the Marrakech suede Vagabond messenger. If we’re spending big, we’re spending on Métier.
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